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N-076

Supelco

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) solution

1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Synonym(s):

4-(Methylnitrosoamino)-1-(3-pyridinyl)-1-butanone, 4-(Methylnitrosamino)-1-(3-pyridinyl)-1-butanone, NNK

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About This Item

Empirical Formula (Hill Notation):
C10H13N3O2
CAS Number:
64091-91-4
Molecular Weight:
207.23
MDL number:
MFCD00274580
UNSPSC Code:
41116107
PubChem Substance ID:
329818458
NACRES:
NA.24

grade

certified reference material

Quality Level

300

form

liquid

feature

Snap-N-Spike®/Snap-N-Shoot®

packaging

ampule of 1 mL

manufacturer/tradename

Cerilliant®

concentration

1.0 mg/mL in methanol

technique(s)

gas chromatography (GC): suitable
liquid chromatography (LC): suitable

application(s)

forensics and toxicology

format

single component solution

storage temp.

−20°C

SMILES string

CN(CCCC(=O)c1cccnc1)N=O

InChI

1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3

InChI key

FLAQQSHRLBFIEZ-UHFFFAOYSA-N

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General description

A Certified Spiking Solution® suitable for use in nicotine testing, environmental monitoring, or clinical and diagnostic testing of nicotine biomarkers by LC-MS/MS or GC/MS. Also known as nicotine-derived nitrosamine ketone, NNK is a potent carcinogen and biomarker of exposure to cigarette smoke. NNK, produced upon the curing of tobacco, is found in a variety of tobacco products including chewing tobacco, snuff, cigarettes, and cigars.

Legal Information

CERILLIANT is a registered trademark of Merck KGaA, Darmstadt, Germany
CERTIFIED SPIKING SOLUTIONS is a registered trademark of Merck KGaA, Darmstadt, Germany
Snap-N-Shoot is a registered trademark of Cerilliant Corporation
Snap-N-Spike is a registered trademark of Merck KGaA, Darmstadt, Germany

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Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

Target Organs

Eyes

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

49.5 °F - closed cup

Flash Point(C)

9.7 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Xuemin Qian et al.
Carcinogenesis, 34(4), 841-849 (2012-12-15)
The main reasons for the failure of most chemopreventive agents during clinical trials are poor in vivo bioavailability and dose-limiting side effects. One potential approach to surmount these problems in lung cancer chemoprevention trials could be direct delivery of agents
Kent-Man Chu et al.
Current pharmaceutical design, 19(1), 5-10 (2012-09-07)
Cigarette smoke has always been the single most preventive cause of death in the world. In 2011, over 460,000 died from cigarette smoke-related diseases in US. The detrimental effects of cigarette smoke on human beings are due to the presence
Lucie Skarydova et al.
Drug metabolism letters, 6(3), 174-181 (2013-01-22)
Tobacco smoking is the most widely known cause of human cancer-related death worldwide. NNK is one of the proved human carcinogens contributing to the development of several types of cancer. The carcinogenic effect of NNK depends on the metabolic pathway.
Zhifeng Sun et al.
Biochemical and biophysical research communications, 435(3), 472-476 (2013-05-16)
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is one of the major carcinogens in tobacco. NNK has been associated with various cancers in tobacco users, especially lung cancer. However, the effects of NNK on cytotoxic T lymphocytes (CTLs), the cells responsible for destrcution of maligant
Chi-Jung Chung et al.
Toxicology letters, 216(1), 16-22 (2012-11-13)
Gene polymorphisms of the 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism-related enzymes-cytochrome P450 (CYP) monooxygenase 2A13 (CYP2A13) and UDP-glucuronosyltransferases (UGT)-2B7 could contribute to the levels of NNK-related metabolites in urine, thereby increasing the susceptibility to urothelial carcinoma (UC). Therefore, our study aimed to evaluate
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